Work Completed: 01.22.

09
Work Submitted: 02.03.09

Synthesis 0732: Isolating Caffeine from Tea

Abstract

Caffeine was extracted from instant tea and purified by recrystallization. The yield was
determined to be 1.2152 % of caffeine per one gram of instant tea.

Introduction

In this experiment, caffeine will be extracted from instant tea. The caffeine will be
purified by recrystallization and the percent mass of caffeine per gram of instant tea will be
determined. Students will perform the following experiment to determine how much
caffeine is in one gram of a typical caffeinated beverage such as instant tea.

Objectives:

1. To extract caffeine from tea

2. To perform a vacuum filtration
3. To separate layers from a crude extract
4. To purify caffeine by recrystallization
5. To determine the percent of caffeine per gram of instant tea

Descriptions

Caffeine is a natural product belonging to the alkaloid group. Caffeine is a stimulant

and has some undesirable side effects where an individual has a physical dependence to
this chemical. Many of the earliest isolated pure compounds from plants were alkaloids
because of the ease of isolation. This is because a nitrogen atom generally makes the
compound basic and the compound exists in the plant as a salt. Most alkaloids are
extracted with water or weak acid and recovered as crystalline material by treatment with
base. The following flow chart outlines a typical extraction of the stimulant caffeine from
its natural alkaloid state.

Organic Chemistry II, Lab Report 2 Page 1

 Flow chart:
Isolating Caffeine from Tea

Tea + dichloromethane Extract Tea + dichloromethane

(DCM) + 2M NaOH (DCM) + 2M NaOH

Separate

Organic Layer - Aqueous Layer –

Discard
DCM + Caffeine NaOH

Distill
Collect Excess DCM Caffeine + small
amount of DCM

Evaporate
Remaining DCM into the
Crude Caffeine
atmosphere
Add 2 – propanol, Heat (hv)

Caffeine +
2-propanol

Cool

Cooled Caffeine +
2-propanol

Add Hexane, Filter

Caffeine Crystals

Structural formulas of some xanthine alkaloids:

O H O O O
H
H N H
N N N N
N N N

O N N N N
O N N O N O N
H
Xanthine Caffeine Theophyline Theobromine

Organic Chemistry II, Lab Report 2 Page 2

 Materials:

Figure 1 Distilling Apparatus

Thermometer

Water Out

Condenser

Water In

Hickman Still Head

Conical Vial

Sand Bath
Heat Source
5 6 5 6
4 7 4 7

3 8 3 8

2 9 2 9
1 10
1 1 10

Stirring Apparatus

Students will use the distilling apparatus to separate the caffeine and DCM.

Table 1 List of Materials and Equipment

List of Materials List of Equipment

1. Instant tea To isolate purified 1. Round bottom To mix tea, NaOH, and
caffeine flask DCM
2. Dichloromethane To extract the 2. Phase separation To separate the
caffeine paper caffeine from the tea,
3. 2M NaOH To extract the NaOH, DCM mixture
caffeine 3. Hirsch funnel To filter crystals
4. 2-propanol To recrystallize with adapter
5. Hexane To wash the purified 4. Hot plate For hot water bath
crystals
6. Anhydrous sodium Drying agent
sulfate

Organic Chemistry II, Lab Report 2 Page 3

Procedural Steps:
1. Mix tea
2. Separate aqueous and organic layers
3. Distill
4. Evaporate to crude caffeine
5. Dissolve and recrystallize
6. Filter purified caffeine
7. Record mass of crystals

Data and Results

Table 2 Data and Results

Mass Instant Tea 1.0122 g

Mass Recovered Caffeine Crystals 0.0123 g

Calculations:

(Eq. 1)

= 1.2152 %

Discussions and Conclusions

By calculation, the amount of caffeine per one gram of instant tea was determines to
be 1.2152 %. This data may be imprecise because during the extraction of caffeine,
emulsions may have occurred. This happens when an organic compound of one liquid in a
second liquid and the first compound will not mix such as a case with water and oil.
Because of this, during phase separation, a arbitrary amount of caffeine was separated
depending on how gentle students shook the mixture.

In this experiment, caffeine was extracted from instant tea using an aqueous
solution of sodium hydroxide and hexane. Sodium Hydroxide was used to prevent the
extraction of acidic compounds called tannins from the tea leaves. Caffeine is more soluble
in an organic solvent, which is why dichloromethane was used instead of water to extract
the organic solvent and separate it from glucose, tannins, and other water soluble
compounds.

Organic Chemistry II, Lab Report 2 Page 4

References

McMurry, John, Organic Chemistry 7th edition, Thompson Learning Inc. Books/Cole 2008.

Silberman, Robert. “Isolating Caffeine from Tea,” page 65-73, Signature Lab Series, CHE
2403, Cengage Learning. Mason, Ohio: 2008.

Wu, Jennifer CHE 2403 Signature Lab Series Page 65-73.

Organic Chemistry II, Lab Report 2 Page 5